A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation

An operationally simple, open-air, and efficient light-mediated Minisci C-H alkylation method is described, based on the formation of an electron donor-acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method does not require a photocatalyst, an external single electron transfer agent, or an oxidant additive. Achieved under mildly acidic and open-air conditions, the reaction incorporates primary-, secondary-, and tertiary radicals, including bicyclo[1.1.1]pentyl (BCP) radicals, along with various heterocycles to generate Minisci alkylation products in moderate to good yields. Additionally, the method is exploited to generate a stereo-enriched, hetereoaryl-substituted carbohydrate.

Automated summary

In this study, a simple, open-air, and efficient light-mediated Minisci C-H alkylation method is described, which is based on the formation of an electron donor-acceptor complex. Unlike previous protocols, this method does not require a photocatalyst, single electron transfer agent, or oxidant additive. The reaction can proceed under mildly acidic and open-air conditions, and it yields moderate to good amounts of Minisci alkylation products.